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Ultrasound-activated atom-economical approach to the synthesis of highly substituted pyrrolidin-2-ones through a four-component Ugi/5-endo-trig intramolecular radical cyclization reaction

An efficient and diversity-oriented access to functionalized pyrrolidin-2-ones through an Ugi reaction of readily available starting materials with a subsequent transformation is described. A two-step reaction sequence of a four-component Ugi reaction and an intramolecular radical-cyclization reacti...

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Main Authors: Rahimi, Atena Nashta (Author) , Ghazvini, Helya Janatian (Author) , Balalaie, Saeed (Author) , Rominger, Frank (Author) , Tejeneki, Hossein Zahedian (Author) , Bijanzadeh, Hamid R. (Author)
Format: Article (Journal) Editorial
Language:English
Published: 13.03.2020
In: Synlett
Year: 2020, Volume: 31, Issue: 09, Pages: 871-877
ISSN:1437-2096
DOI:10.1055/s-0040-1707997
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1055/s-0040-1707997
Verlag, lizenzpflichtig, Volltext: http://www.thieme-connect.de/DOI/DOI?10.1055/s-0040-1707997
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Author Notes:Atena Nashta Rahimi, Helya Janatian Ghazvini, Saeed Balalaie, Frank Rominger, Hossein Zahedian Tejeneki, Hamid R. Bijanzadeh
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Summary:An efficient and diversity-oriented access to functionalized pyrrolidin-2-ones through an Ugi reaction of readily available starting materials with a subsequent transformation is described. A two-step reaction sequence of a four-component Ugi reaction and an intramolecular radical-cyclization reaction leads to the chemo- and regioselective formation of a single product with high atom economy and good to high yields. The radicalization of the pseudopeptides generated from the first step by a cavitational mechanism produces the key intermediate for the ultrasound-activated formation of γ-lactams as the final products by β-Michael addition. Among the advantages of this approach are its use of cavitation bubble implosion as an exclusive path to radicalization of the polyfunctional Ugi adduct, its high selectivity, and its short reaction times.
Item Description:Gesehen am 31.03.2021
Physical Description:Online Resource
ISSN:1437-2096
DOI:10.1055/s-0040-1707997

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